3-[Methyl-(1H-pyrrole-3-sulfonyl)-amino]-propionic acid ethyl ester | 232945-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-[Methyl-(1H-pyrrole-3-sulfonyl)-amino]-propionic acid ethyl ester
• 英文别名: ethyl 3-[methyl(1H-pyrrol-3-ylsulfonyl)amino]propanoate
• CAS: 232945-07-2
• 化学式: C₁₀H₁₆N₂O₄S
• 分子量: 260.314
• InChiKey: GVKVLENGIRSQGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[Methyl-(1H-pyrrole-3-sulfonyl)-amino]-propionic acid ethyl ester 在 80 percent-PPA 作用下， 反应 1.0h， 生成 2-methyl-3,4,5,7-tetrahydro-2H-pyrrolo[3,4-f][1,2]thiazepin-5-one 1,1-dioxide
  参考文献：
  名称：

  重温吡咯的磺化：磺化位置正确吗？

  摘要：

  如教科书所述，发现三氧化硫-吡啶配合物对吡咯及其1-甲基衍生物的磺化作用产生了3-磺化的吡咯，但没有2-磺化的吡咯。用甲基磺酸氯代甲基硅烷基酯代替1-甲基-2-三-正丁基锡烷基吡咯，然后用碳酸氢钠水溶液淬灭。NaHCO 3还产生1-甲基吡咯-3-磺酸钠，而不是2-磺酸钠。

  DOI：

  10.1016/s0040-4039(00)01127-8
• 作为产物：
  描述：

  3-(甲基氨基)丙酸乙酯 、 3-pyrrolesulfonyl chloride 生成 3-[Methyl-(1H-pyrrole-3-sulfonyl)-amino]-propionic acid ethyl ester
  参考文献：
  名称：

  重温吡咯的磺化：磺化位置正确吗？

  摘要：

  如教科书所述，发现三氧化硫-吡啶配合物对吡咯及其1-甲基衍生物的磺化作用产生了3-磺化的吡咯，但没有2-磺化的吡咯。用甲基磺酸氯代甲基硅烷基酯代替1-甲基-2-三-正丁基锡烷基吡咯，然后用碳酸氢钠水溶液淬灭。NaHCO 3还产生1-甲基吡咯-3-磺酸钠，而不是2-磺酸钠。

  DOI：

  10.1016/s0040-4039(00)01127-8

文献信息

• Pyrrolothiazine and pyrrolothiazepine compounds having serotonin-2 receptor antagonistic and alpha-1-blocking action
  申请人：Suntory Limited

  公开号：US06331623B1

  公开（公告）日：2001-12-18

  A pyrrolesulfonamide compound having formula (I) wherein the ring P represented by &agr; is a pyrrole ring having structure &bgr; or &psgr; wherein A represents alkylene, alkenylene or alkynylene; and Y represents a group &dgr; in which W represents CH, C═ or N; m stands for 0 or 1 when W is CH or N, or m stands for 1 when W is C═; B represents a specific divalent group; E1 and E2 each independently represents H or lower alkyl; and D represents an aromatic hydrocarbon group or heterocyclic group; l stands for 0 or 1; the dashed line indicates the presence or absence of a bond; and, when the bond is present, Z2 is not present and Z1 represents H but, when the bond is absent, Z1 represents H and Z2 represents OH or Z1 and Z2 are combined together to represent O or a group NOR5, in which R5 represents H, or alkyl, aralkyl or aryl; and R represents H, alkyl, cycloalkyl, cycloalkyl-alkyl or aralkyl. The compound (1) has been improved in potency, selectivity to receptors other than serotonin-2 receptors, toxicity, side effects and/or the like over medicines reported to date and equipped with a &agr;1-blocking action and serotonin-2 receptor antagonistic action in combination.

  一种具有以下式(I)的吡咯磺酰胺化合物，其中表示为α的环P是具有结构β或ψ的吡咯环，其中A表示烷基，烯基或炔基; Y表示具有W代表CH，C═或N的δ基团; 当W为CH或N时，m为0或1，当W为C═时，m为1; B表示特定的二价基团; E1和E2各自独立地表示H或较低的烷基; D表示芳香族烃基或杂环基团; l为0或1; 虚线表示键的存在或不存在; 当键存在时，Z2不存在且Z1表示H，但当键不存在时，Z1表示H且Z2表示OH或Z1和Z2组合在一起表示O或NOR5基团，其中R5表示H，或烷基，芳基烷基或芳基; R表示H，烷基，环烷基，环烷基烷基或芳基烷基。该化合物(1)在与α1-阻滞作用和血清素2受体拮抗作用相结合的同时，已经在药物的效力、对血清素2受体以外的受体的选择性、毒性、副作用等方面得到了改善。
• PYRROLOTHIAZINE AND PYRROLOTHIAZEPINE COMPOUNDS HAVING SEROTONIN-2 RECEPTOR ANTAGONISTIC AND ALPHA-1-BLOCKING ACTION
  申请人：SUNTORY LIMITED

  公开号：EP0970089A2

  公开（公告）日：2000-01-12
• US6331623B1
  申请人：——

  公开号：US6331623B1

  公开（公告）日：2001-12-18
• US6583296B2
  申请人：——

  公开号：US6583296B2

  公开（公告）日：2003-06-24
• [EN] PYRROLOTHIAZINE AND PYRROLOTHIAZEPINE COMPOUNDS HAVING SEROTONIN-2 RECEPTOR ANTAGONISTIC AND ALPHA-1-BLOCKING ACTION<br/>[FR] COMPOSES DE PYRROLOTHIAZINE ET PYRROLOTHIAZEPINE PRESENTANT UNE ACTION ANTAGONISTE DU RECEPTEUR DE SEROTONINE-2 ET BLOQUANT ALPHA-1
  申请人：SUNTORY LTD

  公开号：WO1999033841A2

  公开（公告）日：1999-07-08

  A pyrrolesulfonamide compound having formula (I) wherein the ring P represented by (α) is a pyrrole ring having structure (β) or (γ) wherein A represents alkylene, alkenylene or alkynylene; and Y represents a group (δ) in which W represents CH, C= or N; m stands for 0 or 1 when W is CH or N, or m stands for 1 when W is C=; B represents a specific divalent group; E1 and E2 each independently represents H or lower alkyl; and D represents an aromatic hydrocarbon group or heterocyclic group; $(1,3)$ stands for 0 or 1; the dashed line indicates the presence or absence of a bond; and, when the bond is present, Z2 is not present and Z1 represents H but, when the bond is absent, Z1 represents H and Z2 represents OH or Z1 and Z2 are combined together to represent O or a group NOR5, in which R5 represents H, or alkyl, aralkyl or aryl; and R represents H, alkyl, cycloalkyl, cycloalkyl-alkyl or aralkyl. The compound (1) has been improved in potency, selectivity to receptors other than serotonin-2 receptors, toxicity, side effects and/or the like over medicines reported to date and equipped with α1-blocking action and serotonin-2 receptor antagonistic action in combination.